New York Holiday Homes with Staff

We selected the 472 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in New York

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops.

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

This Hamptons home does island life the modern way. In the mornings, hit up the local farmers’ markets and seafood shops.

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

Immersed in a sanctuary of trees, this rustic cabin invites you to enjoy a serene retreat in the Catskill Mountains. Set across five acres and just a six-minute drive from the charming town of Roscoe, there’s everything you could need to feel inspired and renewed by the majestic beauty of this special environment.

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, Nora Ephron and John Steinbeck.


We selected the top 3% holiday homes in New York Holiday Homes with Staff

Explore the 472 most perfect homes in our collection

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Most popular homes in New York

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

The Great Harvest

The Great Harvest

  • 34 guests

  • 10 bedrooms

Coolbaugh Township, Monroe County

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Rise with the Sun

Rise with the Sun

  • 20 guests

  • 8 bedrooms

Pleasant Valley, New York

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

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Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in NY, New York, U.S.? If so, you've definitely come to the right place. Reach out to our expert team who will happily arrange for staff to be present at your home in NY, New York, U.S. as an addition to your booking. Our Plum Guide homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short extended stay. Should you need anything, our friendly team is on hand 24/7, so just ask.

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